{{Short description|MDMA metabolite}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | drug_name = HMA | image = 4-Hydroxy-3-methoxyamphetamine structure.svg | image_class = skin-invert-image | width = 225px | caption =
<!-- Clinical data --> | pronounce = | tradename = | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = | class = Serotonin–norepinephrine–dopamine releasing agent | ATC_prefix = | ATC_suffix =
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<!-- Identifiers --> | CAS_number = 13026-44-3 | CAS_supplemental = | PubChem = 197139 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID = 170725 | UNII = UW5V6G007J | KEGG = | ChEBI = 173516 | ChEMBL = 1347 | NIAID_ChemDB = | PDB_ligand = | synonyms = HMA; 3-Methoxy-4-hydroxyamphetamine; MHA; 3-''O''-Methyl-α-methyldopamine
<!-- Chemical data --> | IUPAC_name = 4-(2-aminopropyl)-2-methoxyphenol | C=10 | H=15 | N=1 | O=2 | SMILES = CC(CC1=CC(=C(C=C1)O)OC)N | StdInChI = 1S/C10H15NO2/c1-7(11)5-8-3-4-9(12)10(6-8)13-2/h3-4,6-7,12H,5,11H2,1-2H3 | StdInChIKey = GPBOYXOSSQEJBH-UHFFFAOYSA-N }}
'''4-Hydroxy-3-methoxyamphetamine''' ('''HMA'''), also known as '''3-''O''-methyl-α-methyldopamine''', is an active metabolite of 3,4-methylenedioxymethamphetamine (MDMA).<ref name="delaTorreFarréPizarro2004">{{cite journal | vauthors = de la Torre R, Farré M, Roset PN, Pizarro N, Abanades S, Segura M, Segura J, Camí J | title = Human pharmacology of MDMA: pharmacokinetics, metabolism, and disposition | journal = Therapeutic Drug Monitoring | volume = 26 | issue = 2 | pages = 137–144 | date = April 2004 | pmid = 15228154 | doi = 10.1097/00007691-200404000-00009 }}</ref><ref name="RietjensHondebrinkWesterink2012">{{cite journal | vauthors = Rietjens SJ, Hondebrink L, Westerink RH, Meulenbelt J | title = Pharmacokinetics and pharmacodynamics of 3,4-methylenedioxymethamphetamine (MDMA): interindividual differences due to polymorphisms and drug-drug interactions | journal = Critical Reviews in Toxicology | volume = 42 | issue = 10 | pages = 854–876 | date = November 2012 | pmid = 23030234 | doi = 10.3109/10408444.2012.725029 }}</ref><ref name="LuethiKolaczynskaWalter2019">{{cite journal | vauthors = Luethi D, Kolaczynska KE, Walter M, Suzuki M, Rice KC, Blough BE, Hoener MC, Baumann MH, Liechti ME | title = Metabolites of the ring-substituted stimulants MDMA, methylone and MDPV differentially affect human monoaminergic systems | journal = Journal of Psychopharmacology | volume = 33 | issue = 7 | pages = 831–841 | date = July 2019 | pmid = 31038382 | doi = 10.1177/0269881119844185 | pmc = 8269116 }}</ref> It is substantially less potent than MDMA or 3,4-methylenedioxyamphetamine (MDA) as a monoamine releasing agent ''in vitro''.<ref name="Blough2008">{{cite book | vauthors = Blough B | chapter = Dopamine-releasing agents | veditors = Trudell ML, Izenwasser S | title = Dopamine Transporters: Chemistry, Biology and Pharmacology | pages = 305–320 | date = July 2008 | isbn = 978-0-470-11790-3 | oclc = 181862653 | ol = OL18589888W | publisher = Wiley | location = Hoboken [NJ] | doi = | url = https://books.google.com/books?id=QCagLAAACAAJ | chapter-url = https://bitnest.netfirms.com/external/Books/Dopamine-releasing-agents_c11.pdf }}</ref><ref name="Yubero-LahozAyestasBlough2012">{{cite journal | vauthors = Yubero-Lahoz S, Ayestas MA, Blough BE, Partilla JS, Rothman RB, de la Torre R, Baumann MH | title = Effects of MDMA and related analogs on plasma 5-HT: relevance to 5-HT transporters in blood and brain | journal = European Journal of Pharmacology | volume = 674 | issue = 2–3 | pages = 337–344 | date = January 2012 | pmid = 22079770 | pmc = 3253888 | doi = 10.1016/j.ejphar.2011.10.033 }}</ref> Nonetheless, HMA has been found to induce the release of serotonin, norepinephrine, and dopamine with {{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}} values of 897{{nbsp}}nM, 694{{nbsp}}nM, and 1450–3423{{nbsp}}nM, respectively, and hence acts as a lower-potency serotonin–norepinephrine–dopamine releasing agent (SNDRA).<ref name="Blough2008" /><ref name="Yubero-LahozAyestasBlough2012" /> The predicted log P of HMA is 0.6.<ref name="PubChem">{{cite web | title=3-O-Methyl-Alpha-Methyldopamine | work = PubChem | publisher = U.S. National Library of Medicine | url=https://pubchem.ncbi.nlm.nih.gov/compound/197139 | access-date=14 November 2024}}</ref>
== See also == * Substituted amphetamine * 4-Hydroxy-3-methoxymethamphetamine (HMMA) * 3,4-Dihydroxyamphetamine (HHA; α-methyldopamine) * 3,4-Dihydroxymethamphetamine (HHMA; α-methylepinine) * 2,4,5-Trihydroxyamphetamine (THA) * 2,4,5-Trihydroxymethamphetamine (THMA) * 3,4-Dimethoxyamphetamine (DMA) * 3,4-Dihydroxymethcathinone (HHMC) * 4-Hydroxy-3-methoxymethcathinone (HMMC)
== References == {{Reflist}}
{{Monoamine releasing agents}} {{Phenethylamines}}
{{DEFAULTSORT:Hydroxy-3-methoxyamphetamine, 4-}}
Category:Methoxyphenethylamines Category:Phenols Category:Psychedelic drug metabolites Category:Serotonin-norepinephrine-dopamine releasing agents Category:Substituted amphetamines
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